Bis (triorganosilyl) phosphate compositions

ABSTRACT

Disiloxy derivatives of fluoroalkyl acid phosphates of the general formula ARE DISCLOSED AS CORROSION INHIBITORS FOR FLUOROSILICONE LUBRICANTS.

Unite States Patent [151 3,694,479 Groenhof 1 Sept. 26, 1972 [54] BIS(TRIORGANOSILYL) PHOSPHATE 3,441,537 4/1969 Lengnick ..260/448.2 N XCOMPOSITIONS 3,441,585 4/1969 Brown ..260/448.2 N 3 385 822 5/1968 Brown..260/448.2 N X 72 1 t E. D. f, 1 l 1 Gmnh Md and Mmh 3,639,239 2/1972Groenhof ..260/448.2 N x [73] Assrgnee: Dow Corning Corporation,Midland, 3,631,088 12/1971 Lengnick et a1. ...260/448.2 N

Mich.

- Primary Examiner-Tobias E. Levow 1 [22] F1 ed March 1971 AssistantExaminer-P. F. Shaver [21] App]. No.2 129,181 Attorney-Robert T.Fleming, Jr., Lawrence R.

Related US. Application Data Hobey, Harry D. Dmgman and Norman E. Lewis[62] Division of Ser. No. 858,886, Sept. 17, 1969, [57] ABSTRACTDisiloxy derivatives of fluoroalkyl acid phosphates of 52 US. Cl......260/488.2 N, 252/499, 260/448.2 E the general fmmula [51] Int. Cl...C07f 7/08 xwmmwmhmoSiCHzCHZRM [58] Field of Search ..260/448.2 N 1][56] References Cited are disclosed as corrosion inhibitors forfluorosilicone UNITED STATES PATENTS lubricants- 3,418,240 12/1968 Myers..260/448.2 N X 3 Claims, No Drawings R, is a perfluoroalkyl radical ofno more than 10 carbon atoms;

R is a lower alkyl radical of no more than six carbon atoms or a phenylradical;

X is a hydrogen or fluorine atom;

n is an integer having a value of from 1 to 16; and

m is an integer having a value of from 2 to 24.

As described above, R; can be any perfluoroalkyl radical, such as -CF CF and so on thru C, F The radicals can be straight-or branched chain.The same or different R, radicals can be bonded in the same siliconatom.

Thus, included within the scope of the invention are compounds of theformulas and precurser is prepared by the reaction of ammonia with 65silanes of the formula (R CH CH )R SiCl. The fluoroalkylphosphoriccompounds are well-known and are commercially available.

reacting fluoroal- The compounds of the invention are useful ascorrosion inhibiting additives to organopolysiloxane fluids.Dimethylpolysiloxanes, phenylmethylpolysiloxanes andtrifluoropropylmethylsiloxanes are representative of such siloxanes.Generally, from 0.005 to 5 weight percent concentrations of the disiloxycompounds in the fluids is sufficient to obtain the desired inhibitionof corrosion.

The following examples are illustrative and not limiting of theinvention, which is properly delineated in the claims.

EXAMPLE 1 A mixture of fluoroalkyl phosphates (43.5 grams) of theformulas R(CF CH OPC(OH) and H(CF Cl-I OPO(OH) was dissolved in 50milliliters of diethylether. A slight excess of {CF CH CH (CI-l SiNl-Uwas added to the ether solution. Ammonia was generated immediately.The reaction mixture was stirred for one hour at room temperature andthen heated at ether reflux temperature for one hour. The reactionmixture was vacuum distilled to obtain a percent yield of H(CF CHOP(O){OSi(Cl-l Cl-l CH 2 having a boiling point range for the differentspecies of l25-l5 1 C./0.l mm Hg.

EXAMPLE 2 To demonstrate its utility as a rust inhibitor in lubricants,various amounts of the product of Example 1 were added to3,3,3-trifluoropropylmethylpolysiloxane which had a viscosity of 300 cs.at 25 C. The inhibitorcontaining fluids were tested in accordance withASTM D-665A. Test results are listed below:

in Fluid Lu ant (wt. Soluble Results 01 yes pass 0.05 yes pass 0.10 yespass 0.20 yes pass 1.0 yes pass The fluorosilicone lubricant was testedwithout the addition of compounds within the scope of the invention andfailed the test.

That which is claimed is:

l. Compositions of the formula e a O in which R, is a perfluoroalkylradical of no more than 10 carbon atoms;

R is a lower alkyl radical of no more than six carbon atoms or a phenylradical;

X is a hydrogen or a fluorine atom;

n is an integer having a value of from 1 to 16; and

m is an integer having a value of from 2 to 24.

2. Compositions in accordance with claim 1 wherein R; is a CF radical.

3. Compositions in accordance with claim 2 of the formula H( CF ,CHOP(O) OSi(Cl-l )CH CH CF in which m equals 4 or 6.

2. Compositions in accordance with claim 1 wherein Rf is a -CF3 radical.3. Compositions in accordance with claim 2 of the formulaH(CF2)mCH2OP(O)(OSi(CH3)CH2CH2CF3)2 in which m equals 4 or 6.